My time in the US was quickly coming to a close. After four and a half months stateside, it was time time hit the road once again. But first, I needed one last hit of family time to tide me over for the long stretch of travel ahead. So for my final week in the country, I made my way back to Martha’s Vineyard for some quality bonding with a star studded cast — my mom and her man, my sis and her guy, and my beloved cousin Kirsten, who flew in from Chicago.

Overall, it was a blissfully relaxed week with plenty of time for long lunches, yoga classes, runs and walks out to the nearby lighthouse, and generally enjoying each others’ company. Kirsten and Olivia’s boyfriend Oliver were Martha’s Vineyard newbies, and as always, we delighted in showing them around the island we’re still so excited to be calling our new home.

So what kept us busy? The bad news was the weather was quite iffy throughout the week, leaving our beach time fairly limited. The good news was, we had a laid back crew more than happy to make the most of it. As usual, we were regulars at State Beach, where Olivia and Oliver had a clear difference of opinion regarding whether or not the temperature was bathing suit appropriate.

But on one special day, when our family friend Ashley and her boyfriend J came to visit from their place on Cape Cod, my mom showed us a new favorite stretch of sand: Great Rock Bight Preserve. With limited parking and a long, steep walk down to the beach, it’s quite the hidden gem. While we had a particularly cloudy day, Olivia and I braved the cold waters to swim out to the famous rock in the distance for bragging rights and a spot of sister bonding time. I love discovering new corners of the Vineyard and this is one nook I’ll absolutely be returning to — assuming we can snag one of the parking spots.

When storms kept us inside, we amused ourselves indoors with a bit of backgammon and competitive puzzling.

And, of course, we ate. We’ve had a long run of racking up new favorite Vineyard eateries with tons of hits and very few misses, but this time we added two the list of places we weren’t impressed with. Sand Bar and Grille in Oak Bluffs and The Shanty in Edgartown were both too mediocre to ever warrant a return meal, though we all agreed we’d return to either for an atmospheric drink or two.

One clear winner, as usual? Sharky’s Cantina! Oliver happens to be a bit of a food snob and Olivia reveled in telling me that he had turned his nose up at my favorite Mexican joint when they walked by before my arrival. And I reveled equally as he ate his words alongside with his monster-sized taco salad. Sharky’s Cantina: turning skeptics into believers since the advent of free guacamole refills.

And a week in Martha’s Vineyard wouldn’t be a week in Martha’s Vineyard without nightly ice cream runs (and blurry selfies to wash them down.)

The highlight of the week, however, was a unanimous hit. One evening, we decided to splurge on a private party of epic proportions, a sunset sail with Witch of Endor. The beautiful former Taiwanese fishing vessel was under the lovingly helmed by Captain Pascal, who handled our boisterous crew with a smile.

Our group of eight (Ashley and J stuck around for this adventure!) came prepared with a cooler full of drinks in order to properly toast the sunset. We had serious balance practice juggling our drinks as the boat listed in the wind and we ran around the boat snapping photos and pointing out various landmarks we identified along the shore.

There were lots of laughs all around.

It was the perfect evening with so many lovely details — Captain Pascal giving J a spin behind the wheel, the delicious platter of gourmet treats we completely devoured, and a bit of lighthearted family teasing.

All too soon, the sun dipped below the horizon, and we headed back to shore.

I can’t recommend a trip with Witch of Endor more highly. Split among our group of eight, it was a reasonable price to pay for such a special experience (two hour sails start at $350) and the fact that we were able to bring along our own booze made it into quite the party. In fact, we decided to keep the energy up as soon as we arrived back at the house.

While the grown ups called it a night after a round of shots, the kids headed out on the town. Well, as much of a town as there is on weeknight on a small island not quite yet into peak summer season. We started with cocktails at the new outpost of Beetlebung in Oak Bluffs, a chic new lounge addition to the local nightlife scene.

After a swing by the Lampost, we realized that we were in a tight spot: we were starving, and considering the late hour, island eateries were shut down tight. Olivia refused to accept defeat though, and grabbed Kirsten for a tipsy mission to scour snacks. We dissolved into hysterics when not fifteen minutes later she came running up Circuit Avenue, pizza boxes in hand, triumphant whoops all around. Turns out she had caught a friendly local pizza chef closing down the kitchen for the night, and via some impressive miming through the glass door she managed to convey the depth of both her hunger desperation and their shared love for pizza.

He handed over the last pies of the night free of charge, and even posed for what I’d call the clear winner of Best Selfie of the Summer.

It was a beautiful week indeed. But the best is yet to come — my first stateside Independence Day in six years! Stay tuned…

Have you managed to squeeze in plenty of family time this summer? What have you and yours been up to?

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Please Note: We received a small media discount from Witch of Endor Sailing in order to write this review. As always, you receive my honest opinions regardless of any discounts of comps.

wow that looks like fun! I’m telling ya it makes such a difference to live by a beach. We have cook outs and bonfires, but only got to go from Ohio to Alabama or NC once a year as a kid which was always the best. Even now, I love family vacays to the beach. Your mom has got a sweet new spot there!Rachel of Hippie in Heels recently posted..This is India! (ten)

I was just admiring your photo editing skills – your photos are always full of pretty pastels!- when I got to the part about horrible weather. Like wow, you even know how to add sunshine to your photos!Silvia recently posted..Searching For Komodo Dragons in Indonesia

Oh my gosh, I can’t believe I forgot to address that in my post. I guess I thought I did in my New Orleans posts, but maybe Oliver hadn’t earned being a named character on the blog yet 🙂 Um yes, it is indeed real. And too cute for words.

So I already see comments about Ollie and Ollie – seriously, how much cuter can they get?!

Looks like a nice send off before your next jaunt through SE Asia. I’ve had similar bonding times with family here in Japan so this post gave me the warm fuzzies 🙂Michelle | Lights Camera Travel recently posted..Love, Sex, Relationships and Travel

Ah! This looks so lovely. I’ve never been to Martha’s Vineyard, but your posts definitely make me want to go. (And side note – I love seeing that other people resort to/enjoy puzzles as a rainy day activity like I do!)Susan recently posted..Getting Wild at the Keenesburg Animal Sanctuary

We are a family of huge puzzle nerds! We do massive multi-thousand piece ones every Thanksgiving, and my sister and I got pretty competitive over them this summer too! We also got very into the backgammon. It’s a great alternative to sitting in front of the TV on quiet evenings (though I adore doing that too!)

Love that your sister and her boyfriend have matching name – so cute! I want to demolish that taco salad – best I have ever had was in Vancouver at Granville Island marketKatie @ The World on my Necklace recently posted..How I save money for travel

That sailing trip looks like great fun! What a lovely sunset! And the boat Witch of Endor looks beautiful! It even has a cat, so cute! 🙂 Ah, I miss sailing. We used to go sailing at home, but hope to get the chance to cacth up on our sailing skills again soon, maybe in the Caribbeans this autumn.Maria from Nerd Nomads recently posted..How To Stay Healthy While Traveling

I'm a New York native who left my home to explore the world slowly and thoroughly. I’m just a little obsessed with photography, scuba diving, and reading guidebooks to countries I have no immediate plans to visit.